Convenient syntheses of 5-O- and 3,5-di-O-(β-d-galactofuranosyl)-d-galactofuranose
Benzoylation of d-galactono-1,4-lactone with 2.2 mol of benzoyl chloride, at -23°, gave the 2,6-dibenzoate (2, 62%). Tin(IV) chloride-catalyzed glycosylation of 2 with 1,2,3,5,6-penta-O-benzoyl-α,β-d-galactofuranose (1) afforded 2,6-di-O-benzoyl-5-O-(2,3,5,6-tetra-O-benzoyl-β-d-galactofuranosyl)-d-g...
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1990
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| Acceso en línea: | Registro en Scopus DOI Handle Registro en la Biblioteca Digital |
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| LEADER | 05721caa a22007817a 4500 | ||
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| 001 | PAPER-586 | ||
| 003 | AR-BaUEN | ||
| 005 | 20230518202956.0 | ||
| 008 | 190411s1990 xx ||||fo|||| 00| 0 eng|d | ||
| 024 | 7 | |2 scopus |a 2-s2.0-0025714097 | |
| 024 | 7 | |2 cas |a 3,5-di-O-(beta-galactofuranosyl)-galactofuranose, 129728-10-5; 5-O-beta-galactofuranosyl-galactofuranose, 129728-07-0; Disaccharides; Trisaccharides | |
| 040 | |a Scopus |b spa |c AR-BaUEN |d AR-BaUEN | ||
| 030 | |a CRBRA | ||
| 100 | 1 | |a de Lederkremer, R.M. | |
| 245 | 1 | 0 | |a Convenient syntheses of 5-O- and 3,5-di-O-(β-d-galactofuranosyl)-d-galactofuranose |
| 260 | |c 1990 | ||
| 270 | 1 | 0 | |m de Lederkremer, R.M.; Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Ciudad Universitaria, Pabellon II, 1428 Buenos Aires, Argentina |
| 506 | |2 openaire |e Política editorial | ||
| 504 | |a McNeill, Wallner, Hunter, Brennan, (1987) Carbohydr. Res., 166, pp. 299-308 | ||
| 504 | |a Notermans, Veeneman, van Zuylen, Hoogerhout, van Boom, (1988) Mol. Immunol., 25, pp. 975-979 | ||
| 504 | |a Bennett, Bhattacharjee, Glaudemans, (1985) Mol. Immun., 22, pp. 251-254 | ||
| 504 | |a Mendonça-Previato, Gorin, Travassos, (1980) Infect. Immun., 29, pp. 934-939 | ||
| 504 | |a Gander, Jentoft, Drewes, Rick, (1974) J. Biol. Chem., 249, pp. 2063-2072 | ||
| 504 | |a Schnaidman, Yoshida, Gorin, Travassos, (1986) J. Protozool., 33, pp. 186-191 | ||
| 504 | |a de Lederkremer, Casal, Alves, Colli, (1980) FEBS Lett., 116, pp. 25-29 | ||
| 504 | |a du Mortier, Varela, de Lederkremer, (1989) Carbohydr. Res., 189, pp. 79-86 | ||
| 504 | |a Marino, Varela, de Lederkremer, (1989) Carbohydr. Res., 190, pp. 65-76 | ||
| 504 | |a Gorin, Spencer, 5-O-β-D-GALACTOFURANOSYL-D-GALACTOSE FROM GALACTOCARALOSE (1959) Canadian Journal of Chemistry, 37, pp. 499-502 | ||
| 504 | |a Fernandez Cirelli, Sznaidman, Varela, de Lederkremer, (1983) Tetrahedron, 39, pp. 313-316 | ||
| 504 | |a Bock, Pedersen, (1983) Adv. Carbohydr. Chem. Biochem., 41, pp. 27-66 | ||
| 504 | |a D'Accorso, Thiel, Schüller, (1983) Carbohydr. Res., 124, pp. 177-184 | ||
| 504 | |a Hanessian, Banoub, (1977) Carbohydr. Res., 59, pp. 261-267 | ||
| 504 | |a Bundle, Lemieux, (1976) Methods Carbohydr. Chem., 7, pp. 79-86 | ||
| 504 | |a Lerner, (1972) Methods Carbohydr. Chem., 6, pp. 131-134 | ||
| 504 | |a van Heeswijk, Visser, Vliegenthart, (1977) Carbohydr. Res., 59, pp. 81-86 | ||
| 504 | |a Sugawara, Nakayama, Ogawa, Synthetic studies on glycosidic phytotoxins. Part III. Synthetic studies on derivatives of 5-O-.BETA.-D-galactofuranosyl-D-galactofuranose. (1986) Agricultural and Biological Chemistry, 50, pp. 1557-1561 | ||
| 520 | 3 | |a Benzoylation of d-galactono-1,4-lactone with 2.2 mol of benzoyl chloride, at -23°, gave the 2,6-dibenzoate (2, 62%). Tin(IV) chloride-catalyzed glycosylation of 2 with 1,2,3,5,6-penta-O-benzoyl-α,β-d-galactofuranose (1) afforded 2,6-di-O-benzoyl-5-O-(2,3,5,6-tetra-O-benzoyl-β-d-galactofuranosyl)-d-galactono-1,4-lactone (4, 70%), HO-3 of which was benzoylated to give 5. The structure of 4 was confirmed by its conversion into crystalline β-d-Galf-(1→5)-d-Gal-ol (8). Reduction of the lactone function of 5 with di-isoamylborane followed by debenzoylation gave β-d-Galf-(1→5)-d-Galf (7). A by-product of the condensation of 1 with 2 was characterized as 2,6-di-O-benzoyl-3,5-di-O-(2,3,5,6-tetra-O-benzoyl-β-d-galactofuranosyl)-d-galactono-1,4-lactone (9), which was converted, as for 5, into β-d-Galf-(1→3)[β-d-Galf-(1→5)]-d-Galf (13). © 1990. |l eng | |
| 536 | |a Detalles de la financiación: Universidad de Buenos Aires | ||
| 536 | |a Detalles de la financiación: We thank CONICET (Consejo National de Investigaciones Cientificas y TCc-nicas), the University of Buenos Aires, and UNDP/World Bank/WHO Special Programme for Research and Training in Tropical Diseases for financial support. and UMYMFOR (CONICET-KEN, Buenos Aires) for the microanalyses. | ||
| 593 | |a Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Ciudad Universitaria, Pabellon II, 1428 Buenos Aires, Argentina | ||
| 690 | 1 | 0 | |a 3,5 DI O (BETA GALACTOFURANOSYL) GALACTOFURANOSE |
| 690 | 1 | 0 | |a 3,5-DI-O-(BETA-GALACTOFURANOSYL)-GALACTOFURANOSE |
| 690 | 1 | 0 | |a 5 O BETA GALACTOFURANOSYL GALACTOFURANOSE |
| 690 | 1 | 0 | |a 5-O-BETA-GALACTOFURANOSYL-GALACTOFURANOSE |
| 690 | 1 | 0 | |a DISACCHARIDE |
| 690 | 1 | 0 | |a TRISACCHARIDE |
| 690 | 1 | 0 | |a ARTICLE |
| 690 | 1 | 0 | |a CARBOHYDRATE ANALYSIS |
| 690 | 1 | 0 | |a CHEMISTRY |
| 690 | 1 | 0 | |a MOLECULAR GENETICS |
| 690 | 1 | 0 | |a SYNTHESIS |
| 690 | 1 | 0 | |a CARBOHYDRATE SEQUENCE |
| 690 | 1 | 0 | |a CHEMISTRY |
| 690 | 1 | 0 | |a DISACCHARIDES |
| 690 | 1 | 0 | |a MOLECULAR SEQUENCE DATA |
| 690 | 1 | 0 | |a SUPPORT, NON-U.S. GOV'T |
| 690 | 1 | 0 | |a TRISACCHARIDES |
| 700 | 1 | |a Marino, C. | |
| 700 | 1 | |a Varela, O. | |
| 773 | 0 | |d 1990 |g v. 200 |h pp. 227-235 |k n. C |p Carbohydr. Res. |x 00086215 |w (AR-BaUEN)CENRE-301 |t Carbohydrate Research | |
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| 856 | 4 | 0 | |u https://doi.org/10.1016/0008-6215(90)84193-X |y DOI |
| 856 | 4 | 0 | |u https://hdl.handle.net/20.500.12110/paper_00086215_v200_nC_p227_deLederkremer |y Handle |
| 856 | 4 | 0 | |u https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00086215_v200_nC_p227_deLederkremer |y Registro en la Biblioteca Digital |
| 961 | |a paper_00086215_v200_nC_p227_deLederkremer |b paper |c PE | ||
| 962 | |a info:eu-repo/semantics/article |a info:ar-repo/semantics/artículo |b info:eu-repo/semantics/publishedVersion | ||
| 963 | |a VARI | ||
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